‘How do I ask my boss to let me work remotely?’

More workers are moving away from office life. Here's how to make a business case to work remotely

As the space between work and not-work becomes ever more blurred, questions about how to do this thing we plug away at for 30 or 40 or 70 hours a week become all the more expansive. In Work Flow, we delve into the novel dilemmas created by the new ways we work, as well as timeless questions about ethics, gender assumptions, and toxic work situations (and how to escape them). How we work is an important component of how we live—and we’re here to help you do better at both.

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I’ve been living in a very large, expensive city for most of my adult life. I’ve also been working in the same industry since graduation, gradually making my way up the food chain. I finally have a decent salary and title, but I haven’t been able to save much money over the years due to the high costs of rent and general life needs in my city. I’ve been thinking a lot about making the move to a smaller, less expensive city that’s about two hours away, where I could more easily save enough to buy an apartment. But I love my company and job and don’t want to start over. What’s the best way to broach working remotely from this new city to my boss? 

You’re living in the right time to do this. What might have seemed madness in years past is the norm in a lot of industries. A little more than 8 million people, or 5 percent of the U.S. workforce, did their jobs from home in 2017, according to census data. This isn’t just an American phenomenon, either—remote work is transforming business culture in Europe as well. Along with the fact that technology has helped eliminate much of the need to convene in an office regularly, there are studied benefits to working remotely, including boosted productivity and a higher talent-retention rate. Stanford professor Nicholas Bloom has a TED talk that’s worth watching as you prepare yourself to make the ask. His research found that working from home led to a 22 percent increase in productivity at one company, along with improved work satisfaction and a lower attrition rate (by half). 

I very much suggest noting those statistics in a conversation with your manager! But more about that in a bit. Let’s take it step-by-step. 

How to ask your manager to work remotely 

Step 1: Do your research

Start with your company. It sounds like you’ve been there for a while, and you love it. So look and ask around. Is there a precedent at your company for people working remotely, whether it’s once a week or full-time? If anyone does regularly work from home, talk to them about how they arranged to do that, and how they’ve managed the transition. If you’ve got people to point to and a successful program for this at your company, you’re going to have a much easier road than if you’re the very first employee to make a case for it. 

Of course, there’s a first for everything. You can blaze this trail—but to do so, you’ll have to make a strong proposal. Gather stats that show how letting employees work remotely is good not only for them but also good for the company overall. And paint a clear picture of how seamless it will be to have you transition to remote work. 

Step 2: Understand your (and their) negotiating points

As you build your case, you’ll need to identify your points of leverage, and the points of leverage your company has on you.

First, identify your bottom line: Are you confident that you’re going to make this move anyway, or will you only do it if you can keep your job? Are you willing to walk away from the job you have for the city you want to move to? Would you consider changing your employment status with the company—e.g., becoming a contractor rather than a full-time employee? 

Also, realize that if you are granted the opportunity to work remotely, there is a chance that it won’t work out for the long term—your manager may agree to let you try it but then find that after a few months it’s too disruptive to the team. Prepare yourself for that scenario before making the ask.

If you are willing to make the move and walk away from your job if they say no to your request, you might consider searching for a new role as a backup plan. If you have a competing job offer, you could present it to your company as leverage—but also bear in mind this could backfire, and they could tell you to just take the other offer. Also, realize that you are likely getting paid a premium to work in an expensive city, so you may have to take a lower salary if you move. Your company will likely know this, too. 

Step 3: Lay out the logistics

For you, working remotely might mean being able to save money in this exciting new location or eliminating your commute, but what your manager needs to know is the logistical stuff that matters to them, such as: How are you going to get your work done and continue to be a valuable part of the team?

To help make your case, gather all of the pertinent information that assures them of that, based on your desired city. It should include things like: 

  • Will you be able to come into the office with any regular cadence? Perhaps one day per week, two days per month, or the like?
  • Will you be able to come into the office for large/important meetings as well as conferences, reviews, and events?
  • Will your working hours change? 
  • How will you keep in regular communication with your manager and the team? Perhaps you’ll send a status email at the end of each day, or at the end of the week, depending on how hands-on your manager is. 
  • How will you navigate the challenges of collaborating remotely with colleagues?

Explain how you’re going to tackle any of the potentially negative implications of working remotely, and be prepared to speak to how not being in the office will impact your day-to-day work. Basically, the more you can avoid disrupting your current work arrangement (unless it’s clearly to make it better), the more likely you are to get a yes.

Step 4: Build and present a business case

If you’ve been at your spot for a while (long enough to get a promotion and presumably some positive reviews), you’re in a better position to make this request. Up your chances of getting a yes by putting together a business case for yourself, including answers to the following:

  1. What value do you deliver to the company, in quantifiable terms?
    • Revisit the goals or metrics you are responsible for delivering to the company, and remind your manager what you contribute to the business in material terms. 
    • What unique skills or institutional knowledge do you have that would be costly for your company to replace if you were to leave? 
  2. How will your working remotely actually improve the company’s bottom line? Include any statistics on increased productivity and accountability. Refer back to Nicholas Bloom!
  3. What will this look like in practice, and how will you offset any inconveniences or negative impacts of working remotely? (Refer to the notes you created above.)
  4. How will you measure whether the arrangement is working or not, and the timeline on which you’ll assess it? 

Once you have your proposal together, present it to your manager and have an honest conversation. Make your case: State your value, state the value this arrangement will bring to the company, walk through the logistics of what it will look like, and suggest how you’ll be held accountable for continued good performance. Once you’ve presented your piece, give your manager space to process it. They will likely take some time to get back to you—especially if they need to consult a manager above them, or even HR. Regardless, expect some negotiation. 

Some people really do love working from home. Others can’t stand it and immediately feel isolated and lethargic. If you do get the green light, try these seven strategies for staying inspired as you embark on your working remotely adventure. 

Jen Doll is a journalist and author of the memoir Save the Date: The Occasional Mortifications of a Serial Wedding Guest. Her writing has appeared in the Atlantic, Harper’s Bazaar, the New York Times, and other publications.

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